问题：请问Tf2O是什么？
类型：求助 (悬赏分:3分)
提问：linzeran
等级：▲
版块：分析化学(wangsui,maqinghe,peiliang,)
信誉：83%
回复：3
阅读：6532
时间：2005-03-24 21:23:48 编辑加入/取消收藏订制/取消短消息举报该贴

请问Tf2O是什么？是什么的缩写？

回复人：molecule,▲▲▲ (知道更多，学到更多。) 时间：2005-04-04 10:28:29 编辑	1楼
- trifluoro methanesulfonic acid anhydride + CF3-S(=O)2-O-S(=O)2-CF3, "Tf2O" 可以介绍个网站给你。 http://www.chemie.fu-berlin.de/cgi-bin/acronym

回复人：mipman,▲ (色谱分析和有机合成人员) 时间：2005-04-13 18:26:37 编辑

2楼

http://www.thieme-connect.com/ejournals/html/synlett/doi/10.1055/s-2003-45005

Trifluoromethanesulfonic (triflic) Anhydride

Introduction
Trifluoromethanesulfonic (triflic) anhydride [(CF3SO2)2O; Tf2O] has proved to be a versatile reagent in organic synthesis over the last few decades. [1-3] Due to the excellent leaving group properties of the triflate group, Tf2O finds its use in the conversion of various compounds to triflates which can be transformed into other useful products. Detailed studies have established triflates to be some 2 ?10 [4] to 2 ?105 times more reactive than the comparable tosylates. [1]

The anhydride is best prepared by distillation of triflic acid from excess P2O5. [5] Stang found that yields can be considerably increased by using P2O5 premixed with an equal volume of celite. The pure anhydride is a colourless liquid that is stable for long periods, insoluble in water, does not fume in air and hydrolyses slowly over several days at room temperature. The liquid boils at 81 癈 at 760 torr pressure. The reagent is also commercially available.

(A) The reaction of aliphatic esters with aliphatic and aromatic nitriles in presence of Tf2O affords 4-alkoxypyrimidines. This 璻eaction proceeds through the intermediacy of alkoxy (trifloxy) carbenium ions [6] and leads to isoquinolines in case of arylacetic acid esters. [7] A similar reaction with ketones offers a broad scope for the preparation of functionalised pyrimidines. [8]

(B) The iminium and iminotriflates derived from the treatment of secondary and tertiary amides has opened up broad avenues for transformations of the amide functionality. These salts are versatile reagents that can react with various N-, O- and S-nucleophiles, thereby transforming amide group into other functionalities. [9]

(C) Tf2O has been utilised as a mild activation reagent in 璙ilsmeyer-Haack formylation. Less nucleophilic aromatics can be formylated with DMF/Tf2O. [10]

(D) a-Trifluoromethylsulfonamido furans, an important class of compounds, have recently been prepared by Tf2O-mediated cyclisation of ketoamides and 5-hydroxy substituted pyrrolidinones. [11]

(E) Tf2O is used extensively in carbohydrate chemistry, frequently for glycosylation. Recently a novel sulfide- and sulfoxide-mediated dehydrative glycosylation technique employing Tf2O has been developed. [12]

(F) In hypervalent iodine chemistry, PhIO-Tf2O finds its use in the preparation of 1,4-disubstituted benzene derivatives. The extreme reactivity of the above complex even towards non-activated benzene derivatives affords (p-phenylene)bis(aryliodonium) ditriflates. This subsequently leads to the products. [13]

References
1 Stang PJ, Hanack M, Subramanian LR,Synthesis 1982, 85

2 Ritter K,Synthesis 1993, 735

3 Baraznekok IL, Nenajdenko VG, Balenkova ES,Tetrahedron 2000, 3077

4 Su TM, Sliwinski WF, Schleyer PV,J. Am. Chem. Soc. 1969, 91: 5386

5a Gramstad T, Hazeldine RN,J. Chem. Soc. 1956, 173

5b Gramstad T, Hazeldine RN,J. Chem. Soc. 1957, 4069

6 Mart韓ez AG, Fer醤dez AH, 羖varez RM, Vilchez MD, Guti閞rez ML, Subramanian LR,Tetrahedron 1999, 55: 4825

7 Mart韓ez AG, Fer醤dez AH, Vilchez MD, Guti閞rez ML, Subramanian LR,Synlett 1993, 229

8 Mart韓ez AG, Fer醤dez AH, Jim閚ez FM, Mart韓ez PJ, Martin CA, Subramanian LR,Tetrahedron 1996, 52: 7973

9a Amidines: Charlette AB, Grenon M,Tetrahedron Lett. 2000. 41: p.1677

9b Thiazolidines: Charlette AB, Chua P,J. Org. Chem. 1998. 63: p.908

9c Esters: Charlette AB, Chua P,Synlett 1998. p.163

9d Cyclic ortho esters: Charlette AB, Chua P,Tetrahedron Lett. 1997. 38: p.8499

9e Thioamides: Charlette AB, Grenon M,J. Org. Chem. 2003. 68: p.5792

10 Mart韓ez AG, 羖varez RM, Barcina JO, Cereo SM, Vilar ET, Fraile AG, Hanack M, Subramanian LR,J. Chem. Soc., Chem. Commun. 1990, 1571

11a Padwa A, Rashatasakhon P, Rose M,J. Org. Chem. 2003, 68: 2609

11b Padwa A, Rashatasakhon P, Rose M,J. Org. Chem. 2003, 68: 5139

12a Garcia BA, Gin DY,J. Am. Chem. Soc. 2000, 122: 4269

12b Nguyen HM, Chen Y, Duron SG, Gin DY,J. Am. Chem. Soc. 2001, 123: 8766

12c Honda E, Gin DY,J. Am. Chem. Soc. 2002, 124: 7343

13a Kitamura T, Furuki R, Nagata K, Taniguchi H, Stang PJ,J. Org. Chem. 1992, 57: 6810

13b Kitamura T, Furuki R, Nagata K, Zheng L, Taniguchi H,Synlett 1993, 193

13c Kitamura T, Furuki R, Taniguchi H, Stang PJ,Mendeleev Commun. 1991, 148

回复人：admin,★ (论坛管理员-欢迎大家访问化学化工论坛) 时间：2005-04-13 21:46:00 编辑	3楼
接受答案了。

得分人：mipman-2,molecule-2,

问题讨论没有结束...

您尚未进入本论坛,登录之后才可以回贴

6msec